MATCHPlay — Hosted by Thad Miller, MATCHPlay explores the parallels between building a strong golf game and planning a successful business transition. Each episode features insights, stories, and strategies to help you stay on course—whether you're on the green or planning your next big move.
Most owners think their business is worth what they've decided it's worth. Then they try to sell it and find out the hard way that dependency, the thing that made the business run smoothly for years, is the same thing that's now scaring buyers off. On this episode of MATCHplay, Thad Miller sits down with Ed Mysogland, Managing Partner of Indiana Business Advisors and author of the upcoming book Done Deal, to break down two of the most overlooked realities of selling a business: owner dependency and the real structure behind the number on a term sheet.
Ed has closed nearly 2,400 transactions over three decades, all from the seller's side. He's seen every version of the deal that looked great on paper and fell apart in diligence, and every owner who thought the sale price was the whole story until they got to the fine print.
This episode is for any business owner who's thought about selling, is getting ready to sell, or just wants to understand what buyers are really evaluating.
What You'll Learn:
• Why dependency on the owner is one of the fastest ways to kill a deal, regardless of industry
• How to spot dependency risk in your own business before a buyer does
• Why the headline price on a term sheet is only one line of the actual deal
• What earnouts, employment agreements, and staff outcomes really mean for your bottom line
• How to think about a sale from the seller's side, not just the buyer's
About the Guest:
Ed Mysogland is the Managing Partner of Indiana Business Advisors, an Indiana business brokerage and M&A advisory firm with nearly 2,400 transactions closed. He is the author of Done Deal (releasing September 2026), a guide to the exit process written entirely from the seller's perspective, and the host of Defenders of Business Value, a podcast for advisors and owners who take business value and future business sales seriously. He lives in Carmel, Indiana with his wife and two daughters.
🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162
🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078
📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod
19 Jun 2026
Selling a Business You Plan to Stay In with Michael Bosway
What does it actually feel like to sell a business you've spent decades building, and then stay?
In this episode of MATCHplay, Thad Miller sits down with Michael Bosway, longtime leader of City Securities Corporation, a firm with nearly a century of history and a reputation built on generations of relationships. After more than 30 years with the company, including serving as CEO, Mike led City Securities through its sale to Stifel Financial Corp., one of the fastest-growing national brokerages in the country.
But Mike didn't walk away. He stayed. And so did much of his leadership team. This conversation goes beyond the transaction. It's about how a business earns its reputation over time, how you know when selling is the right move even when you're not forced to, and what it means to choose a buyer you're willing to build with long after the deal closes.
If you're a business owner thinking about a future sale, or trying to understand what life on the other side of a transaction actually looks like, this episode is worth the full round.
What You'll Learn:
-What made City Securities a durable, respected firm across nearly 100 years
-How industry changes like regulation, scale, and competition shift the case for selling
-How to evaluate buyers when you plan to stay on after the acquisition
-Why cultural alignment can matter as much as financial terms
-What owners misunderstand about life after the deal, especially if they remain involved
-How to know whether selling is a proactive decision or a reactive one
About the Guest:
Michael Bosway served as CEO of City Securities Corporation, an Indiana-based financial services firm with nearly a century of history. He led the company's sale to Stifel Financial Corp. and continued in a leadership role following the acquisition, giving him a rare perspective on what it means to sell a business and remain accountable for what comes next.
🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3Ji...
🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matc...
📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits.
12 Jun 2026
Inside the Private Equity Playbook with Pete Munson
What does private equity actually look for when they buy a business?
In this episode of MATCHplay, Thad Miller sits down with Pete Munson, an operator and advisor who has spent years working alongside private equity groups on acquisitions, growth, and value creation.
Pete has seen deals from the inside. What gets attention, what gets passed on, and what ultimately determines whether a business becomes a success story or a missed opportunity. He breaks down the real evaluation process, what separates a business that gets serious offers from one that gets overlooked, and where most founders misread the game before they even sit down at the table.
This conversation is for any business owner who has ever wondered how private equity actually thinks, or who wants to build something worth buying one day.
What You'll Learn:
-What private equity looks for the moment they see a business for the first time
-The non-negotiables that have to be present for a deal to move forward
-How buyers weigh the numbers against the people running the business
-What separates businesses that get strong offers from those that get passed on
-Why deals that look good on paper sometimes fall apart, and where the breakdown usually happens
-What founders misunderstand about the ultimate goal of private equity after a deal closes
-What to think through before entering any PE process, and who is a good fit versus who probably isn't
About the Guest:
Pete Munson is the Managing Director at Cardinal Equity Partners, where he works closely with private equity groups on acquisitions, growth strategy, and value creation. He brings a practitioner's perspective to how deals are evaluated, structured, and ultimately won or lost, and what business owners need to understand long before the process begins.
🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162
🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078
📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod
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Spotify
5.0 / 5
3 ratings
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